Located directly on the city's famed Michigan Avenue, The Allerton is a historic hotel dripping in style. Its Italian Renaissance-inspired exterior is immediately recognizable among the sleek glass-and-chrome structures along Chicago's main thoroughfare. Inside, the 1920s building flaunts sophisticated decor that Frommer's describes as a "glam, Art Deco-inspired look."

Travelzoo Tip: Visit the weekend of Aug. 17 and check out the city's popular -- and free -- Air and Water Show. Guests can walk to Oak Street Beach to watch the impressive display of planes zoom by. Or click here for special rates on activities throughout the summer.

Book by July 21.

*Terms/Conditions:
Restrictions may apply. All reservations require credit card guarantee at time of booking. 24 hours prior to arrival cancellation required to avoid a penalty of one nights room and tax. There's an extra person fee of $25 for each additional person. Rollaway beds are $25 per night; cribs are complimentary.